Home Vacation Rentals By Owner In Cudjoe Key, FL

Showing 180 Of 287 Vacation Rentals
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$196.12

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Caravan Park/Campsite

Waterfront RV Lot in Venture Out 416 - 35' Dock, Ocean Access, Pool & Fishing

Cudjoe Key, Florida, United States

Waterfront RV Lot in Venture Out with 35' Seawall, Ocean Access & Resort AmenitiesbrWelcome to your perfect Florida Keys RV escape, located inside the private, gated community of Venture Out on Cudjoe Key. This waterfront RV lot offers direct boating access, a private dock, and full use of one of the most amenity-rich communities in the Lower Keys. Ideal for boaters, anglers, and anyone looking to experience true island living.brThe SpacebrThis 35' x 69' RV lot is thoughtfully positioned along a peaceful canal, offering a relaxing waterfront setting with easy access to open water. The lot features a concrete pad with full hook-ups available, making it ideal for a comfortable and convenient stay in your own RV.brThere is no RV provided with this rental. Guests must bring their own RV.brThe property includes access to water, electric, and sewer connections, allowing for a seamless setup upon arrival. Enjoy the tropical surroundings, ocean breezes, and the simplicity of outdoor island living.brWaterfront Living, Boating & FishingbrThis lot is a dream setup for boaters and anglers, featuring a 35' concrete seawall with the ability to accommodate your 32' boat.brEnjoy quick and convenient access to both:brThe Atlantic Ocean, perfect for offshore and reef fishingbrThe Gulf backcountry, known for flats fishing and calm cruisingbrLocated near Looe Key Reef, one of the most sought-after reef systems in the Florida Keys, offering exceptional snorkeling and diving just a short boat ride away.brAfter a day on the water, relax dockside and take in the peaceful canal views or head out to nearby sandbars for a true Keys experience.brVenture Out also offers a boat ramp and wash-down station, making launching and retrieving your boat easy and efficient.brCommunity Amenities at Venture OutbrVenture Out is one of the most desirable private communities in the Lower Florida Keys, offering:brMarina store with fuel, bait, and essentialsbrBoat ramp and wash-down stationbrOceanfront common area with tiki huts and lounge seatingbrHeated saltwater pool, hot tub, kiddie pool, and swimming lagoonbrTennis courts, pickleball, bocce, and basketballbrPlayground and open green spacesbrPost office and on-site convenience storebrGolf cart-friendly streets throughout the communitybrLocationbrYou're just minutes from local favorites including The Square Grouper, Mangrove Mama's, Kiki's Sandbar, and Boondocks Grille & Draft House, all within a short drive.brKey West is only about 20 minutes away, offering world-class dining, nightlife, shopping, and iconic attractions.brGood to KnowbrMinimum stay: 1 night (7-night minimum during Lobster Mini Season)brThis is an RV lot only – no RV, bedrooms, or bathrooms are provided, however community bath houses are located inside of Venture Out. brGuests must bring their own RVbrGolf cart rentals available: $50/day, subject to availabilitybrVenture Out registration fee: $125 (subject to change), paid directly at arrival (cash or credit card; fees may apply)brParking: 1 vehicle plus 1 RV must fit fully on the lotbrQuiet hours: 10:00 PM to 6:00 AMbrPrimary guest must be 25 years or olderbrPayment & Booking RequirementsbrSigned rental agreement and government-issued ID required after booking. Please reply to the email you receive from us after signing your Rental Agreement with a photo of your ID.brA 4% credit card processing fee applies to credit card paymentsbrReturned e-checks incur a $25 fee and must be re-paid by credit cardbrWhether you're planning days of world-class fishing, boating out to the reef, or simply enjoying the laid-back island lifestyle, this waterfront RV lot offers a prime home base in the Florida Keys.
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$582.75

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Private Vacation Home

Ocean Blue #265 | Open-Water Views, Pet-Friendly 2BR Retreat in Venture Out

Cudjoe Key, Florida, United States

Oceanfront 2BR/2BA in Venture Out with 70' Seawall, Pet-Friendly, Pool, Stunning Views & Island ComfortbrWelcome to Ocean Blue #225, a beautifully positioned 2-bedroom, 2-bath open-water retreat located inside the private, gated community of Venture Out on Cudjoe Key. With sweeping ocean views, a spacious layout, and a 70' concrete seawall, this pet-friendly home is the perfect escape for boaters, families, couples, and anyone craving laid-back Florida Keys living.brThe SpacebrOcean Blue #225 offers a bright, comfortable interior designed for easy island living. Large windows and outdoor seating areas allow you to take in the beautiful open-water views, while the central A/C keeps the home cool after a day in the sun.brThe well-equipped kitchen features plenty of space to prepare meals, complete with a center island for prep and a Black & Decker 12-cup drip coffee maker to start your mornings right. A washer and dryer are also provided for added convenience during your stay.brThe living room is the perfect place to relax and unwind, featuring comfortable seating, a queen sleeper sofa, and a smart TV for movie nights or lazy afternoons.brBedrooms & Sleeping ArrangementsbrPrimary Bedroom: Queen-size bed, smart TV, and private ensuite full bathroom with walk-in showerbrGuest Bedroom: Queen-size bed and smart TVbrLiving Room: Queen-size sleeper sofabrMaximum Occupancy: 6 guestsbrBathroomsbrPrimary Bathroom: Ensuite full bathroom with walk-in showerbrGuest Bathroom: Full bath with tub/shower combinationbrOutdoor Living & Open Water ViewsbrOcean Blue #225 is perfectly situated on open water, offering beautiful sunrise views and the relaxing sounds of the ocean right from your backyard. Enjoy your morning coffee or evening cocktail from the outdoor seating area while taking in the breeze and waterfront scenery.brThe home also features a propane grill on the front porch, making it easy to cook your fresh catch or enjoy dinner at home after a day exploring the Keys.brBoating & Seawall InformationbrThis property features an impressive 70' concrete seawall that can accommodate boats up to approximately 45 feet once repairs are complete.brImportant: The seawall is currently undergoing repairs and is expected to be completed by July 2026. Boating access and dockage will not be available until construction is finished. Guests booking prior to completion should be aware that no boat use or dock access will be possible during this time.brCommunity Amenities at Venture OutbrVenture Out is one of the most sought-after waterfront communities in the Lower Florida Keys and offers guests access to:br80' heated saltwater swimming pool, hot tub, kiddie pool, and saltwater swimming lagoonbrBoat ramp and wash-down stationbrMarina store with fuel, bait, and convenience itemsbrTennis courts, pickleball, bocce, basketball, and playgroundbrOceanfront common areas with thatched umbrellas and lounge areasbrGated security and electric golf cart-friendly streets throughout the communitybrLocationbrLocated on Cudjoe Key, Ocean Blue #225 places you just minutes from excellent local restaurants, bars, and attractions including Square Grouper, Broil, Mangrove Mama's, Kiki's Sandbar, Boondocks Draft House, and the world-famous Looe Key Reef for snorkeling and diving.brYou're also just a short drive from Key West for shopping, dining, and nightlife, while still enjoying the quieter, more peaceful side of the Lower Keys.brPet-Friendly DetailsbrUp to 2 pets are welcome with prior approval and a paid pet fee of $250 per pet. Guests must notify the rental manager at the time of booking if bringing pets.brGood to KnowbrVenture Out registration fee: $125 (subject to change), paid directly to the community at arrival (cash or credit card; processing fees may apply)brParking: 1 vehicle only. Driveway measures approximately 19'1” long x 11'8” wide and must fit entirely within the driveway without street overhangbrQuiet hours: 10:00 PM to 6:00 AMbrStarter supplies provided: A starter supply of essentials is included to get you started. These supplies are plenty for a 1 night stay.brPrimary guest must be 25 years of age or olderbrPayment & Booking RequirementsbrSigned rental agreement and government-issued ID are required after booking. Please reply to the email you receive from us after signing your rental agreement with a photo of your ID.brA 4% credit card processing fee applies to credit card payments.brWhether you're here to soak in open-water views, relax poolside, fish the flats, or simply enjoy the laid-back beauty of the Florida Keys, Ocean Blue #225 offers the perfect island getaway.
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$459.88

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Private Vacation Home

Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking

Cudjoe Key, Florida, United States

Waterfront Modern Home w/ Dock, Ocean Access + Golf Cart | Fishing Paradise | Resort AmenitiesbrbrStay at this beautifully furnished, modern 2BR/ 2 Bath home in the Florida Keys, located in the private, gated community of Venture Out. Clean, well-stocked, and designed for comfort, this home includes a golf cart for easy access around the resort.brbrPerfect for Boaters & Anglers:brbr• Direct ocean access—ideal for serious fishingbr• Private concrete dock with water & electric, fits up to a 29' boatbr• Fish cleaning station on-sitebr• Off-site trailer parking includedbr• World-class fishing nearby: sailfish, mahi (dolphin), marlin, grouper, snapper, tarpon & morebrbrbrWater Adventures:brbr• Easy access to Looe Key Reef for snorkeling & divingbr• Nearby charters for diving, snorkeling, and fishingbr• Snorkel gear provided for guest usebrbrbrResort-Style Amenities:brbr• Private sandy beachbr• Heated pool + kiddie poolbr• Tennis, pickleball, basketball & bocce courtsbr• Marina with gas, boat ramps, wash-down stations & air pumpsbrbrbrExtras Included:brbr• bicyclesbr• golf cartbr• paddleboard & kayakbrbr brbrNearby Attractions:brbr• Key West festivals like Fantasy Fest, Goombay & Hemingway Daysbr• Marathon’s Turtle Hospital & Dolphin Research Center (swim with dolphins)brbrbrImportant Info:brbr• $125 resort registration fee per stay (paid directly to Venture Out at check-in; not an owner fee)br• Security camera located under the house facing the dock (visible above the lockbox)brbrbrbrbrWhy Guests Love This Home:br✔ Direct ocean access + private dockbr✔ Ideal for fishing & boatingbr✔ Golf cart + water gear includedbr✔ Family-friendly resort amenitiesbr✔ Prime Florida Keys locationbrbrBook now and experience the ultimate Florida Keys getaway—perfect for relaxation, adventure, and unforgettable days on the water.
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$533.46

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Private Vacation Home

CUDJOE GARDENS SANCTUARY- 3 BED/ 2 BATH- POOL, SPA, RV HOOK UP, BRING YOUR BOAT

Cudjoe Key, Florida, United States

Welcome to Cudjoe Gardens Sanctuary – Your Perfect Keys Getaway!brbrLocated in the heart of Cudjoe Key, this beautifully appointed 3-bedroom, 2-bathroom home offers everything you need for a relaxing and adventure-filled vacation.brbrSPACIOUS AND COMFORTABLE LIVING! With nearly 1,800 square feet of living space, the home comfortably accommodates families or groups looking to unwind in paradise. You'll enjoy:br- A fully equipped kitchenbr- Bright, open-concept living areasbr- Cozy, coastal décor throughoutbrbrBOATERS DREAM! Bring your boat (up to 42') and dock along the private bulkhead with deep water access to the Atlantic. Just moments away, Cudjoe Gardens Marina offers convenient fuel and boating supplies.br- Room for boat, trailer, RV & 3 vehiclesbr- Garage access includedbr- Easy ocean access – no bridges or boat liftsbrbrOUTDOOR OASIS! Relax and recharge in your own tropical retreat:br- Large heated/chilled pool*br- Spacious sun deck & shaded outdoor seating areabr- Fully fenced yard – great for privacy and peace of mindbr- Located right on a canalbrbrPERFECT LOCATION! Cudjoe Gardens is a guest favorite for a reason! Just a short drive to:brbr- Key West – vibrant nightlife, dining & historybr- Marathon – family attractions & beachesbrbrLocal fishing hotspots – ideal for anglers of all levelsbrbrWhether you're here to fish, relax by the pool, or explore the Keys, Cudjoe Gardens Sanctuary is your home base for the perfect island escape!brbr*Pool heating/chilling available – inquire for details.brbrbrbrHOUSE FULL DETAILS AND AMENITIES…brWelcome to your canal-front retreat!brThis spacious 3-bedroom, 2-bath home boasts an open floor plan filled with natural light, creating a bright and inviting atmosphere. The seamless flow between the living room, dining area, and kitchen makes everyday living and entertaining effortless.brbrThe thoughtfully designed split-bedroom layout offers privacy and comfort, with the primary suite situated on one side of the home and two guest bedrooms on the opposite side—perfect for hosting visitors or long-term guests.brbrTastefully decorated and fully outfitted with user-friendly amenities, this home is ready for you to relax and enjoy the waterfront lifestyle.brbrPROPERTY OVERVIEWbrThis single-level, stair-free home offers the perfect getaway with spacious indoor comfort and a stunning outdoor oasis. Located in a quiet, well-kept residential neighborhood—ideal for extended stays!brbrSLEEPING ARRANGEMENTSbrPrimary Suite: King BedbrGuest Bedroom 1: Queen BedbrGuest Bedroom 2: Bunk Bed (Full on bottom, Twin on top)brbrBATHROOMSbrPrimary Ensuite: Full bath with shower & separate bathtubbrGuest Bathroom: Full bath with shower/tub combobrbrbrOUTDOOR LIVINGbrPrivate Pool with spa and waterfallbrCovered sitting area, multiple sun loungers, and all-day sunbrBoat access: Accommodates 1 boat up to 42' along the bulkhead (note: lifts not available)brbrPARKINGbrSpace for up to 3 cars, 1 boat, and 1 boat trailerbrRV Parking with hookups available for an additional $30/day (must be arranged in advance)brIncludes blackwater hookupbrRV space does not increase max guest count (6 total guests max)brbrPETSbrNo pets allowed—no exceptionsbrbrPOOL HEATING AND COOLINGbrOptional pool heating or chilling available at $20/daybrbrBOOKING & RENTAL RESTRICTIONSbrMinimum stay: 28 daysbrStart date must be the 1st of the monthbrSplit months not allowed unless pre-approved by managementbrBookings not adhering to these rules will be cancelledbrbrCANCELLATION POLICYbr100% refund if canceled 60+ days before check-inbrbrLOCAL MANAGEMENT & CONCIERGEbrEnjoy peace of mind with direct access to a local property manager during your stay for assistance or local recommendations.
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Exceptional(8)

$293.6

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Private Vacation Home

Waterfront 1BR in Venture Out with 35' Dock, Kayaks, Pool & World-Class Fishing

Cudjoe Key, Florida, United States

Waterfront 1BR Cottage in Venture Out with a 35' Dock, Kayaks, Pool, World-Class Fishing & Boating AccessbrWelcome to Pelican's Paradise #507, a beautifully renovated 1-bedroom, 1-bath waterfront cottage located inside the private, gated community of Venture Out on Cudjoe Key. This inviting retreat is ideal for couples, boaters, and anglers looking to enjoy the Florida Keys with direct water access, excellent amenities, and easy island living.brThe SpacebrThis thoughtfully updated home offers an open-concept living area filled with natural light and coastal charm. The modern kitchen features granite countertops, bar-top seating, and a dining area for four, making it easy to enjoy meals at home. Coffee lovers are well covered with a Keurig, French press, and Cuisinart drip coffee maker.brFor added convenience, high-speed Wi-Fi is available throughout the home, and a washing machine and dryer are provided for use during your stay, making longer visits and boating days easy and comfortable. The home is cooled by two mini-split air conditioning systems, allowing for efficient, customizable comfort.brThe living room features a smart TV and provides a comfortable space to relax after a day on the water.brBedrooms & Sleeping ArrangementsbrPrimary bedroom: Queen-size bed and smart TVbrLiving area: Queen-size Murphy bed with privacy screenbrAdditional sleeping: Air mattress availablebrMaximum occupancy: 6 guestsbrBathroombrThe home features one full bathroom with a tub/shower combination, offering a practical and comfortable setup for both quick rinses after a day on the water and relaxed evenings in.brWaterfront Living, Boating & FishingbrPelican's Paradise is a true boater and angler-friendly getaway, featuring a 35' concrete dock that can accommodate boats up to approximately 32 feet, with easy access to open water via a peaceful canal. Conveniently located near Looe Key, one of the most famous reef systems in the Florida Keys, offering world-class snorkeling, diving, and vibrant marine life in crystal-clear waters just a short boat ride away. Picnic Island is a nearby local sandbar popular with locals and visitors. A beautiful place to hang out after a day of fishing.brGuests enjoy world-class fishing opportunities, with convenient access to both:brThe Atlantic Ocean, ideal for offshore and reef fishingbrThe Gulf backcountry, known for exceptional flats and inshore fishingbrThe private dock includes a fish cleaning station, and Venture Out also offers a boat ramp and wash-down station, making it easy to head out early and return with a smooth end-of-day setup.brGuests may also enjoy:brTwo single sit-on-top kayaksbrOne two-person Hobie Cat kayakbrCalm canal views and effortless days on the waterbrAfter a day outdoors, unwind with the propane gas grill, perfect for preparing your fresh catch or an easy island-style dinner.brCommunity Amenities at Venture OutbrVenture Out is one of the most amenity-rich communities in the Lower Florida Keys, offering:brMarina store with fuel, bait, and convenience itemsbrBoat ramp and wash-down stationbrBeautiful stretch of island along the oceanfront with many thatched roof umbrellas and loungers to take in the clean ocean breezes and relaxbrMassive 80' heated saltwater swimming pool, hot tub, kiddie pool, and saltwater swimming lagoonbrTennis courts, basketball, bocce, and pickleballbrOn-site marina store/market and post officebrElectric Golf cart-friendly streets throughout the communitybrLocationbrYou're just minutes from popular local favorites including Square Grouper, Morning Joint, The Bent Prop, Broil, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House with mini golf, all within a 10-minute drive. Key West is only 20 minutes away, offering additional dining, nightlife, and iconic attractions. brGood to KnowbrMinimum stay: 3 nights (7-night minimum during Lobster Mini Season)brStarter supplies provided: A starter supply of toilet paper and paper towels is provided and typically lasts 1–2 daysbrNo pets permitted due to allergies. Hypoallergenic dogs may be considered with prior approval and a $250 pet feebrGolf cart rentals available: $50 per day, subject to availabilitybrVenture Out registration fee: $125 (subject to change), paid directly to the community at arrival (cash or credit card; processing fees apply)brParking: 1 vehicle per unit. Driveway size is 16'L x 12'W. Overflow parking may be available for an additional feebrCommunity rules: Guests must follow all Venture Out rules and regulations, including quiet hours from 10:00 PM to 6:00 AMbrAge requirement: Primary guest must be 25 years of age or olderbrPayment & Booking RequirementsbrSigned rental agreement and government-issued ID required after booking. Please reply to the email you receive from us after signing your Rental Agreement with a photo of your ID.brA 4% credit card processing fee applies to credit card paymentsbrWhether you're here for world-class Atlantic and Gulf backcountry fishing, boating adventures, or relaxed evenings by the water, Pelican's Paradise #507 offers a comfortable, well-equipped home base for your Florida Keys vacation.
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Exceptional(48)

$445.07

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Cottage

**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool

Cudjoe Key, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrTURTLE COVE VIEWS is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expansive open water views from inside the home through the large windows or from your covered porch, with outdoor dining. The private 35-foot boat slip offers easy access to the beautiful waters of the Florida Keys and the home comes with kayaks and a paddleboard for guest use. TURTLE COVE VIEWS is located at Venture Out, a residential community with a heated 80-foot pool with large Jacuzzi and Kiddie Pool, tennis courts, basketball court, bocce courts, swimming lagoon, marina and convenience market with fuel on site and two double wide boat ramps, Recreation Center with billiards, darts, and ping pong, post office and a library. Venture Out enjoys 24 Hour Patrolled Security.brbrTURTLE COVE VIEWS was recently renovated to a high standard, with Smart TV’s in the living room and both bedrooms. The kitchen is fully equipped with every appliance and tool you’ll need to prepare meals from home. This home accommodates up to 6 people in two bedrooms (a King and a Queen) and a queen-sized sleep sofa. You’ll be able to bring your boat to dock on the 35' concrete seawall equipped with dock posts, cleats, fish cleaning table & swim ladder. TURTLE COVE VIEWS is located near open water, so it’s a great place for a swim.brbrThere are some wonderful nearby places to explore, from Bahia Honda Beach (voted one of the top 10 beaches in the U.S.) and the American Shoal Lighthouse to snorkeling off Looe Key. For dinner out, consider the Square Grouper, Mangrove Mama’s and Tonio’s Seafood Shack just up the road. Last but not least, TURTLE COVE VIEWS is just a 25-minute drive to either Key West or Marathon, with all their attractions.brbrAmenities: Patio chairs, fish cleaning station, seawall / boat dockage, kayaks, paddleboard, and BBQ Gas Grill. Central Air Conditioning/Heating, High speed internet, WiFi, Smart TVs in living room and both bedrooms, queen sleeper sofa, full kitchen, microwave, dishwasher, refrigerator/freezer, cooking utensils, linens provided, washer, dryer. Gated private community with Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball, bocce courts and ping pong. Vehicles must be under ten feet (10’) in width and must not exceed forty feet (40’) total length.brbr** This property will accommodate up to 6 adultsbr** Pets Allowed (dogs are not allowed to be walked in the neighborhood) - Max of 2 pets allowed and an additional fee of $200 per pet will applybr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.brbrIMPORTANT NOTE: Venture Out charges a one-time Registration/Resort Fee due upon arrival: $116.28 + $8.72 Tax = $125 for up to 6 people (Credit card cash PAID DIRECTLY TO VENTURE OUT). If you arrive with more than 6 people which is the maximum allowed in the home, you will not be permitted in the park. Venture Out guests are required to submit additional paperwork in advance of arrival, which Last Key will collect and coordinate within the week of your arrival. Guests should be prepared to submit all guest information to comply with HOA requirements.
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Exceptional(8)

$244.16

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Private Vacation Home

Coconut Cottage #653 - Oceanfront Community

Cudjoe Key, Florida, United States

Welcome to Coconut Cottage #653, your charming oasis nestled within the exclusive gated community of Venture Out in Cudjoe Key, FL.brThis cozy vacation rental home offers the perfect retreat for couples or small families seeking relaxation and adventure in the Florida Keys. Step inside to discover a thoughtfully designed space featuring one bedroom and one bathroom, providing comfort and convenience during your stay.brSink into the plush queen bed after a day of exploration, or utilize the two full-sized pullout couches for additional sleeping arrangements. The heart of Coconut Cottage lies in its inviting backyard seating area, complete with a BBQ grill, where you can savor al fresco meals under the swaying palm trees. With free Wi-Fi, you can stay connected while unwinding in this tranquil setting.brPrimary Bedroom: Queen BedbrOther sleeping arrangements: Two full-size sleeper sofas in the Living RoombrHome is equipped with a washer and dryer in the home so you can pack light.brStocked kitchen to cook up some fresh meals and a dining table with seating for 4. There is a Mr. Coffee Drip Coffee Maker at this home for you to enjoy your favorite brew.br​​​​​​​This home is close to all of the amenities at Venture Out.brThis is a pet friendly home that allows up to 2 dogs with a $250 pet fee per pet. Rental manager must be notified at time of booking.brVenture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts.brAdventure beyond the gates for a bite to eat at some of Florida Key s favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki s Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away!brWhether you re a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the water s edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key.brLocated inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 19'L x 12'W. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay.brMain guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee.brSocial Media -br@bluescaperealestatebrYouTube Videos @bluescapevacationsbrBook your stay today and experience the beauty of waterfront living!
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Exceptional(3)

$390.0

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Private Vacation Home

Fin's Hideaway - Venture Out #259

Cudjoe Key, Florida, United States

VO259brFINS HideawaybrCanal Front Home 35' DockagebrBeautiful bay views at this canal front home located only 120' from the main channel. This boaters paradise has a 35' seawall at the intersection of 2 canals for spacious docking and swimming. Conveniences include cleats, fenders, docking whips, a new fillet table, an outdoor shower, and market umbrellas available to set up on the dock posts. Relax on the outdoor covered deck with your morning coffee and in the evening grill your catch while watching the shrimp, snapper and tarpon swimming around the underwater green light. Extra toys stored under the deck: 4 kayaks, SUP, rafts and noodles. Also included: Fast ATT WIFI, Amazon Fire TVs, newly renovated kitchen with blender/smoothie maker, rice cooker, electric skillet, crock pot, coffee maker, knife sharpener, and a bait freezer. The spacious living room has a queen size fold out sofa and a futon. The master bedroom with en suite bathroom has a queen size bed. The guest room has a single over double bunk bed. Washer and dryer are included. Pet friendly must comply with Venture Out Pet Rules & Regulations. brSECURITY DEPOSIT REQUIRED, NO SMOKING,br7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL,brOVERFLOW PARKINGIS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brVO REGISTRATION FEE is $125**DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.br****VEHICLE MAY NOT HANG INTO STREET- GUEST MUST VERIFY PRIOR TO RESERVING****
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Exceptional(32)

$234.64

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Hotel Resort

ISLAND PARADISE

Cudjoe Key, Florida, United States

We have central air,1 bedroom, 1 bathroom with fully stocked kitchen, washer and dryer, dishwasher, toaster, keurig duo coffee maker and much more. Super clean and comfortable! We have a BBQ grill, and large common area in backyard with picnic tables and shade trees. We are not located on the water but our open water views are amazing! Bedroom has king bed and living area has a brand new queen size sleeper sofa featuring a comfortable gel memory foam mattress. There’s a TV in master bedroom as well as in the living room. WI-FI is located in the unit, you don’t have to go to the recreation center for your internet service. Bungalow will sleep 4. There’s a heated community pool, salt water swimming area, tiki huts on the beach, tennis courts, bocce ball, pickle ball, marina with 2 boat launching ramps at no additional charge, grocery store and many activities. This is a great vacation spot with 5 star restaurants 5 minutes away. Bahia Honda State Park is only minutes away with a beautiful beach. We have bicycles, and paddle boards. Looe Key offers an amazing reef and is close by. Lots of sandbars for your enjoyment. Key West is 20 miles away for lots of music, restaurants, beaches, Fort Zachary Taylor, shopping and much more. Lots of music and great restaurants close by. We are located in Venture Out Resort which is a great centralized location. Come join us in the Florida Keys for great fishing, spear fishing, diving, snorkeling hanging at the beach or just hanging out at this amazing resort! This is the perfect vacation spot!br***THERE IS A NON-REFUNDABLE REGISTRATION FEE OF $125 CHARGED BY VENTURE OUT RESORT TO BE PAID AT GATE.Pet fee is $100
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$195.4

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Caravan Park/Campsite

Tropical Waterfront RV lot in Cudjoe Key perfect for your getaway.

Cudjoe Key, Florida, United States

NO Tent Camping permitted.brNO Conversion RVs permitted.brNO RV provided.brbrWelcome to your private slice of paradise in the Florida Keys! This spacious waterfront RV lot in Venture Out on Cudjoe Key is one of the largest in the community, offering plenty of room to comfortably accommodate up to a 45ft RV plus additional parking for your car or truck — with extra space to relax and enjoy. Enjoy beautiful canal-front living with your own 17 ft seawall, perfect for docking your boat, launching kayaks, or simply soaking in the peaceful water views. The lot features tropical landscaping, a fish cleaning station, and multiple seating areas including picnic tables for outdoor dining and entertaining. Located inside the gated Venture Out Resort Community, you’ll have access to a wide range of amenities, including: Heated swimming pool, Jacuzzi/spa, Private boat ramp and marina, Fuel dock and boat wash-down station, On-site convenience store, bait station, Tennis courts, pickleball, and basketball, Playground and recreation areas, and 24-hour gated security. Whether you're fishing, boating, or heading into Key West just 20 minutes away, this lot is the perfect home base for your Keys adventure. After a day on the water, unwind in your own tropical retreat with stunning sunsets, peaceful surroundings, and everything you need for a relaxing getaway. Pet-friendly. Boater’s dream location. True Florida. Keys experience. Come experience why Cudjoe Key is one of the most sought-after destinations in the Lower Keys — we can’t wait to host you!brNo RV provided—please bring your own rig.
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Exceptional(4)

$320.49

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Private Vacation Home

Casa Cudjoe: Tropical Canal Front Retreat on Cudjoe Key, Dockage, Boater's Paradise & Dog-Friendly!

Cudjoe Key, Florida, United States

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Casa Cudjoe, a tropical haven nestled in the enchanting neighborhood of Cudjoe Gardens! brbr brbrThis canal front retreat invites you to experience the epitome of Florida Keys living, with direct dockage granting you swift access to both the serene waters of the Atlantic and the boundless expanse of the Gulf. Gather your loved ones and unwind in the inviting embrace of the screened porch, where cherished moments and laughter unfold against the backdrop of passing boats. Sip on your favorite cocktail and revel in the tranquil rhythm of the waterways. Casa Cudjoe is your gateway to a world of leisure and adventure. Whether you're embarking on aquatic escapades or simply savoring the comforts of your home away from home, every moment is an opportunity to create cherished memories. While this tropical haven offers a wealth of delights on its premises, the allure of the Keys awaits your exploration. A short 30-minute drive takes you to the vibrant heart of Key West, while Marathon's charm beckons just 40 minutes away. Secure your stay at Casa Cudjoe today and uncover the essence of Keys living, where relaxation, natural beauty, and unforgettable experiences come together in perfect harmony. brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1: King Bed, En-Suite Bathroom, Smart TV (no cable/satellite) brbr brbrBedroom 2: Queen Bed, Smart TV (no cable/satellite) brbr brbrBedroom 3: Two Twin Beds, Smart TV (no cable/satellite) brbr brbrLiving Room: Sofa, Three Chairs, Smart TV (no cable/satellite) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- 100' of Dockage (Davits are not for guest use) brbr brbr- Propane BBQ Grill brbr brbr- Parking for a maximum of 3 vehicles (including boat trailers) on the property, the driveway is steep. Recreational Vehicles may not be parked on the property. brbr brbr- Linen's and towels provided brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrPet Policy: Up to one friendly and well-behaved dog 25 LBS or less will be considered with a $10/night pet fee. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit household pet information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. After booking, you'll receive a link to complete the process. brbr brbrNo Smoking: Smoking is strictly prohibited within the property. For the comfort and safety of all guests, please refrain from smoking indoors. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrBoating & Dockage Advisory: Due to bridges and varying water depths, it is your responsibility to ensure that your boat can safely navigate local waters, access the canal, and fit the listed dockage before booking. While we are happy to provide general information based on our knowledge of the area, guests must exercise extreme caution when boating and ensure all activities comply with local regulations. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, two exterior security cameras monitor the property. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.
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$501.95

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Mobile Home

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Cudjoe Key, Florida, United States

Welcome to Conch Hideaway #423, an affordable getaway near Key West-located inside the private, gated community of Venture Out on Cudjoe Key. This cozy 1 bedroom, 1 bathroom retreat offers a simple, relaxed space perfect for guests looking to enjoy the Lower Florida Keys. With peek-a-boo canal views from the backyard and plenty of outdoor seating, you'll feel that island breeze the moment you arrive.brThe SpacebrConch Hideaway is designed for easy island living. The open living area features comfortable seating, a 43'' Smart TV, and a full-size pull-out sofa bed for additional guests.brHigh-speed WiFi is available throughout the home, making it easy to stay connected during your stay.brThe kitchen area includes a two-burner electric cooktop, toaster oven, single-cup coffee maker, and a Black and Decker blender for frozen margaritas after a day on the water. There is no traditional oven. A small dining table with two bar stools offers indoor seating, while the generous outdoor dining space makes it easy to enjoy meals outside in the Keys air. A propane grill is also available for guest use.brTwo window A/C units keep the home cool and comfortable year-round.brBedrooms & Sleeping ArrangementsbrBedroom: Full-size bed with 27'' Smart TVbrDrawn drapery for privacybrLiving area: Full-size sofa bedbrMaximum occupancy: 4 guestsbrBathroombrThe home features one full bathroom with a large walk-in shower.brOutdoor SpacebrEnjoy peek-a-boo canal views from the backyard along with ample outdoor dining and seating space. It is the perfect spot for morning coffee, evening cocktails, or simply unwinding after a day at the pool or on the water.brLaundry facilities are conveniently located just across the street- pay per use.brCommunity Amenities at Venture OutbrVenture Out is one of the most amenity-rich communities in the Lower Florida Keys, offering:brMarina store with fuel, bait, and convenience itemsbrBoat ramp and wash-down stationbrOceanfront stretch with tiki huts and loungersbr80' heated saltwater swimming pool, hot tub, kiddie pool, and saltwater lagoonbrTennis courts, basketball, bocce, and pickleballbrOn-site market and post officebrPay-per-use laundry facilitiesbrGolf cart-friendly streets throughout the communitybrLocationbrYou are just minutes from local favorites including Square Grouper, Morning Joint, The Bent Prop, Broil, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House with mini golf. Key West is approximately 20 minutes away for additional dining, nightlife, and iconic attractions.brGood to KnowbrDog friendly: Up to 2 dogs allowed. $250 non-refundable pet fee per dog.brGolf cart rentals available: $50 per day, subject to availabilitybrVenture Out registration fee: $125, subject to change, paid directly to the community upon arrivalbrParking: 1 vehicle per unit. Driveway measures 21' L x 10' WbrBoat and trailer parking: Overflow parking is available at a first come, first serve basis depending on availability. There are off-site boat/trailer parking options as well.brCommunity rules: Guests must follow all Venture Out rules and regulations, including quiet hours from 10:00 PM to 6:00 AMbrAge requirement: Primary guest must be 25 years of age or olderbrPayment & Booking RequirementsbrSigned rental agreement and government-issued ID required after bookingbrA 4 percent credit card processing fee applies to credit card payments
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$290.2

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Private Vacation Home

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

Cudjoe Key, Florida, United States

Description:brbrBeautiful newer 2 bedroom / 2 bath elevated tropical home near a waterfront common area in Venture Out, an Oceanside residential community (Unit #618). Relax on a large elevated covered deck for outdoor dining and entertaining and a downstairs covered area with high top table, lounge chairs and covered parking. A stainless steel gas grill enhances the outdoor dining. The home can sleep up to 6 adults in comfort.brbrThe open Living area includes a cathedral ceiling, a full kitchen with stainless steel appliances with all dishes, silverware and cooking equipment, a dining room with a table for 6 and a living room.brbrThe living room has a queen size sleeper sofa, chairs and love seat, a 50' Flat Screen Roku TV w/ enhanced cable and DVD game inputs, AM/FM CD player. Also included is a wheeled beverage cart that can be used indoors or on the deck.brbrThe Master Bedroom has a queen bed with a 32' flat screen HD Smart Roku TV w/DVD, a double walk in mirrored closet and a full-size master bathroom with shower, vanity sink, toilet, and towels.brbrThe Guest room has a queen bed, a 40” flat screen Smart Roku HDTV, DVD player, a walk in closet and a 2nd full-sized bathroom with shower, vanity sink, toilet, and towels just a few steps down the hall. Off of this bathroom is a stacked washer and dryer combo for your use.brbrAdditional unit amenities include: Free Use of 4 kayaks, adult and children's bikes, Central Air Conditioning, Free WIFI, Washer/Dryer, Dishwasher, Ceiling fans, Microwave, Regular and K Cup Coffee maker, AM/FM CD player, Ice-maker, Ironing board, iron, hair dryers and beach towels for the pool or beach. brbrThe community amenities include: 24 hour security, Lighted tennis and pickle ball courts, Olympic-sized heated pool, kiddie pool, spa Jacuzzi, ping pong, bocce ball courts, pickle ball, lighted basketball court, children's playground, pool table, darts, Marina complete with 2 ramps, gas, store, ATM and fish cleaning station, boat trailer parking onsite, open water picnic areas, ocean front tiki hut, lending library, post office - and MORE - ALL IN A GATED COMMUNITY with a mixture of RV sites and manufactured homes where you can feel safe and secure.brbrSix bikes (4 adult - 2 child) are provided for your riding pleasure at no extra charge. We also have sports equipment, fishing poles with basic tackle, a cooler and 6 beach chairs and umbrellas for trips to the beach, pool or off site.brbrBring your boat! There is no charge for launching in at the Venture Out Marina (There is a small charge for overnight parking). The Florida Keys have some of the best fishing in the world! (Boat and trailer parking, as available is an additional daily charge by the park.) It is also a great spot for launching Kayaks. You can swim or fish from our open water areas. There are several Tiki Huts on the open water where picnicking is perfect!brbrKEY WEST is a twenty five minute drive down US Route 1. Experience the fabulous SUNSET CELEBRATION every night at Mallory Square. Take a day trip to the Dry Tortugas. DANCE the night away at Hog's Breath Saloon, Sloppy Joe's or one of the many bars of Key West. VISIT the Southernmost point, Hemmingway’s house, Key West Light and Fort Zachary Taylor. Take a sightseeing tour on the Key West Trolley or Conch Train. ENJOY a beautiful sunset cruise, snorkeling, SCUBA diving, fishing, parasailing and so much more. brbrOr you can simply enjoy a good book or the company of your family or spouse on the grounds of the resort.brbrWithin several minutes we have some great restaurants. They include The Square Grouper, Boondocks and Loo Key Restaurant to name a few. Most offer good food, open air dining, reasonable prices and a relaxed atmosphere.brbrThe Marina Store within walking distance in the park stocks many necessities, such as soft drinks, BEER and WINE. The Store also has a 24 hour ATMbrbrSORRY, THIS IS A NO SMOKING / NO PET HOUSE. Smoking is allowed in the lower area (ground level) of the home.brbrThis is a very clean rental unit with numerous amenities offered at a very reasonable rate. You will not be disappointed! We know you will have a marvelous time here in the gorgeous FLORIDA KEYS!brbrPlease note that there is a $125.00 one time per party entry fee for our gated community that you will have to pay at the front gate. brbrDriving Distance: 3 Hours from Miami, and 3 1/2 Hours from FT. Lauderdale. 25 Minutes from Key West and Big Pine Key, home of the famous Key Deer.brbrbrKeywords: Housebr*Free WiFibr*A/Cbr*Outdoor Grill
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$367.17

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Private Vacation Home

Oceanfront 2BR/2BA in Cudjoe Key | 50' Seawall, Dock, Open Porch, Stunning Views

Cudjoe Key, Florida, United States

Welcome to Mariner's Nook #484, a charming 2-bedroom, 2-bath getaway perched at the corner of a canal and open water, offering some of the most stunning views in the Lower Keys. From nearly every window, you'll enjoy expansive ocean vistas that fill the living and dining rooms with endless blue horizons. Outside, a sprawling 50-foot seawall that can accommodate up to a 48' boat provides everything you need for waterfront living, including a fish cleaning table, dock posts, cleats, and a swim ladder for easy access to the water. Relax on the open porch overlooking the ocean, where an outdoor dining table for four sets the scene for sunset meals, or stretch out on the dockside lounge chairs and watch the boats pass by.brInside, the home is thoughtfully designed for comfort with central air conditioning, wireless internet, and cable TV. The master bedroom features a queen bed, while the guest bedroom is equipped with two twin/double bunk beds, making it ideal for families or groups. A washer and dryer add convenience, so you can stay fresh after a day of swimming, boating, or fishing. brThere is a Mr Coffee 12 cup drip coffee maker at this home for you to enjoy your favorite brew. Whether you're seeking a peaceful retreat or an adventurous Keys experience, Mariner's Nook delivers the perfect blend of coastal charm and unforgettable views.brSorry, no pets allowed at this home. brVenture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts.brAdventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kikis Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away! Whether you re a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key.brLocated inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 12'L x 10'W. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay. Main guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee. brbrSocial Media -br@bluescaperealestatebrYouTube Videos @bluescapevacations brBook your stay today and experience the beauty of waterfront living
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